An electronic device may connect to an update server in order to obtain updates for an operating system running on the electronic device. An auto-update module of the operating system may be used to establish a connection to the update server using various proxy servers. A proxy manager module of the operating system may be used to determine which proxy server to use. The proxy manager module may typically be integral with a core part of the operating system, and as a result, may be implemented with the least amount of restriction in accessing and/or modifying the operating system. In other words, as part of the core part of the operating system, the proxy manager module may be considered trustworthy, and have privileged permission to access and/or modify the operating system.